WO2016194887A1 - ショ糖脂肪酸エステルの製造方法 - Google Patents

ショ糖脂肪酸エステルの製造方法 Download PDF

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WO2016194887A1
WO2016194887A1 PCT/JP2016/065971 JP2016065971W WO2016194887A1 WO 2016194887 A1 WO2016194887 A1 WO 2016194887A1 JP 2016065971 W JP2016065971 W JP 2016065971W WO 2016194887 A1 WO2016194887 A1 WO 2016194887A1
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Prior art keywords
fatty acid
sucrose
acid ester
monoester
reaction
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PCT/JP2016/065971
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English (en)
French (fr)
Japanese (ja)
Inventor
径治 木谷
幸生 秋山
英資 栗原
保徳 塚原
治樹 奥村
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マイクロ波化学株式会社
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Priority claimed from JP2015111457A external-priority patent/JP5945756B1/ja
Priority claimed from JP2016027481A external-priority patent/JP5952980B1/ja
Priority claimed from JP2016107204A external-priority patent/JP6276806B2/ja
Application filed by マイクロ波化学株式会社 filed Critical マイクロ波化学株式会社
Priority to KR1020167032211A priority Critical patent/KR20180016919A/ko
Priority to US15/314,553 priority patent/US20170183371A1/en
Priority to DK16801940.4T priority patent/DK3141555T3/da
Priority to CN201680001386.5A priority patent/CN106488925B/zh
Priority to EP16801940.4A priority patent/EP3141555B1/en
Publication of WO2016194887A1 publication Critical patent/WO2016194887A1/ja

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H13/00—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids
    • C07H13/02—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids
    • C07H13/04—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids having the esterifying carboxyl radicals attached to acyclic carbon atoms
    • C07H13/06—Fatty acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H1/00—Processes for the preparation of sugar derivatives

Definitions

  • the present invention relates to a method for producing a sucrose fatty acid ester having a high monoester selectivity.
  • sugar fatty acid esters are produced by transesterifying sugar and fatty acid esters (see, for example, Patent Document 1).
  • sugar fatty acid esters diesters (di-forms), triesters (tri-forms) and the like are produced together with monoesters (mono-forms), but sucrose fatty acid esters (sugar esters) and Since monoesters of sugar fatty acid esters such as glucose fatty acid esters have excellent characteristics, there has been a demand for producing sugar fatty acid esters so that the monoester content is increased.
  • monoesters of sucrose fatty acid esters are known to have antibacterial properties and heat stability.
  • monoesters are used in food additives such as emulsifiers, cosmetics, pharmaceuticals, and the like, there has been a demand for producing sucrose fatty acid esters without odor.
  • the present invention has been made in the above situation, and an object thereof is to provide a method for producing a sucrose fatty acid ester having a high monoester ratio and no odor.
  • the inventors of the present invention irradiate microwaves and heat them so that they are lower than the decomposition temperature of sucrose.
  • the inventors have found that sugar fatty acid esters can be produced and have completed the invention.
  • the present invention is as follows. [1] preparing an aqueous solution containing sucrose and a basic catalyst; A step of producing a sucrose fatty acid ester by mixing an aqueous solution obtained in this step, a fatty acid alkali metal salt, and a fatty acid ester and stirring and heating under reduced pressure, The step of producing the sucrose fatty acid ester has a previous step of removing water from the mixture, and a subsequent step of performing transesterification after the step, In the subsequent step, a method for producing a sucrose fatty acid ester, wherein the mixture is heated by irradiation with microwaves so that the mixture is lower than the decomposition temperature of the sucrose.
  • the method further includes the step of producing a fatty acid alkali metal salt by mixing and heating a fatty acid ester and a solution obtained by dissolving an alkali metal salt in a solvent,
  • the sucrose according to any one of [1] to [3], wherein the fatty acid alkali metal salt used in the step of producing the sucrose fatty acid ester is produced in the step of producing the fatty acid alkali metal salt.
  • sucrose fatty acid ester according to any one of [1] to [4], wherein in the subsequent step, the mixture is heated so that the temperature of the mixture is 25 ° C. lower than the decomposition temperature and lower than the decomposition temperature. Manufacturing method.
  • a sucrose fatty acid ester having a high monoester ratio and no odor is obtained by irradiating with microwaves and heating so as to be lower than the decomposition temperature of sucrose Can be manufactured.
  • Table showing results of Examples and Comparative Examples The graph which shows the time change of the mono-body yield of an Example and a comparative example, and a mono-body weight ratio. Table showing results of Examples and Comparative Examples The graph which shows the time change of the mono-body yield of an Example and a comparative example, and a mono-body weight ratio. Table showing results of Examples and Comparative Examples The graph which shows the time change of the mono-body yield of an Example and a comparative example, and a mono-body weight ratio. Table showing results of Examples and Comparative Examples The graph which shows the time change of the mono-body yield of an Example and a comparative example, and a mono-body weight ratio.
  • Table showing results of Examples and Comparative Examples The graph which shows the time change of the mono-body yield of an Example and a comparative example, and a mono-body weight ratio.
  • Table showing results of Examples and Comparative Examples The graph which shows the time change of the mono-body yield of an Example and a comparative example, and a mono-body weight ratio.
  • the aqueous solution obtained in the step, the fatty acid alkali metal salt produced in the step of producing the fatty acid alkali metal salt, and the fatty acid ester are mixed, stirred under reduced pressure and heated to produce sucrose fatty acid ester.
  • a method for producing a sucrose fatty acid ester has a preceding step of removing water from the mixture and a subsequent step of transesterification after the step. In the subsequent process, the mixture is heated so as to be lower than the decomposition temperature of sucrose by irradiation with microwaves.
  • the fatty acid ester used in the step of producing the fatty acid alkali metal salt may be, for example, a fatty acid alkyl ester or a fatty acid polyhydric alcohol ester.
  • the constituent fatty acid of the fatty acid ester is not particularly limited. For example, it may be a short-chain fatty acid having 7 or less carbon atoms, a medium-chain fatty acid having 8 to 10 carbon atoms, or a long-chain fatty acid having 12 or more carbon atoms.
  • the constituent fatty acid may be, for example, a fatty acid having 8 to 24 carbon atoms, a fatty acid having 8 to 22 carbon atoms, a fatty acid having 8 to 20 carbon atoms, The number may be 8 to 18 fatty acids.
  • the fatty acid may be a saturated fatty acid or an unsaturated fatty acid.
  • the constituent fatty acid of the fatty acid ester may be, for example, a fatty acid ester having at least one selected from saturated fatty acids having 8 to 12 carbon atoms and saturated and unsaturated fatty acids having 14 to 24 carbon atoms as constituent fatty acids.
  • the unsaturated fatty acid may be a monounsaturated fatty acid (monoene fatty acid) or a polyunsaturated fatty acid (polyene fatty acid).
  • fatty acids examples include caprylic acid, capric acid, lauric acid, myristic acid, myristoleic acid, palmitic acid, palmitoleic acid, stearic acid, oleic acid, linoleic acid, linolenic acid, eleostearic acid, arachidic acid, and mead acid.
  • the alkyl group in the fatty acid alkyl ester may be, for example, a linear or branched alkyl group having 1 to 5 carbon atoms.
  • Examples of the alkyl group having 1 to 5 carbon atoms include methyl group, ethyl group, n-propyl group, isopropyl group, cyclopropyl group, n-butyl group, isobutyl group, sec-butyl group, t-butyl group, and cyclobutyl.
  • As the alkyl group for example, a methyl group or an ethyl group is preferable.
  • the polyhydric alcohol in the fatty acid polyhydric alcohol ester may be divalent to hexavalent, for example.
  • examples of the divalent to hexavalent polyhydric alcohol include glycol (ethylene glycol, propylene glycol, butylene glycol, etc.), glycerol (glycerin), pentaerythritol, or sorbitol.
  • the fatty acid ester is not particularly limited.
  • It may be a fatty acid alkyl ester such as ethyl, ethyl caprate, ethyl laurate, ethyl myristate, ethyl palmitate, ethyl palmitate, ethyl stearate, ethyl oleate, or ethyl linoleate, or ethylene glycol fatty acid Ester, propylene glycol fatty acid ester, butylene glycol fatty acid ester, glycerin fatty acid ester, pentaerythritol fatty acid ester, sorbitol fatty acid ester, etc.
  • Fatty acid may be a poly
  • the amount of fatty acid ester used in the step of producing the fatty acid alkali metal salt is not particularly limited, but the fatty acid ester used for producing the fatty acid alkali metal salt is the same as the fatty acid ester used for producing the sucrose fatty acid ester. In the case where sucrose fatty acid ester is produced using a fatty acid ester that has not been reacted in the production of fatty acid alkali metal salt, the conversion rate in the production reaction of fatty acid alkali metal salt is approximately 100%.
  • generating a fatty-acid alkali metal salt may be the same equivalent or more as desired fatty-acid alkali metal salt.
  • the alkali metal salt is an alkali metal salt such as lithium, sodium, or potassium.
  • the salt may be, for example, a hydroxide, carbonate, bicarbonate, hydride, or alkoxide.
  • the alkali metal salt is not particularly limited, and may be, for example, potassium hydroxide, potassium carbonate, potassium hydrogen carbonate, methoxy potassium (potassium methoxide), sodium hydroxide, sodium carbonate, sodium hydrogen carbonate, or sodium methoxide. . These alkali metal salts may be used alone or in combination.
  • the amount of the alkali metal salt used is preferably an amount that can produce the necessary amount of the fatty acid alkali metal salt in the step of producing the fatty acid ester, for example, even if it is equivalent to the desired fatty acid alkali metal salt. Good.
  • the alkali metal salt it is preferable to use potassium hydroxide or sodium hydroxide.
  • the solvent is not particularly limited as long as it can dissolve the alkali metal salt.
  • it may be at least one solvent selected from alcohol, ketone, and water.
  • the alcohol is not particularly limited, but may be, for example, an alcohol having 1 to 5 carbon atoms.
  • Examples of the alcohol having 1 to 5 carbon atoms include methanol, ethanol, propanol (1-propanol), isopropanol (2-propanol), n-butanol, isobutanol, sec-butanol, tert-butanol, n-amyl alcohol, Mention may be made of sec-amyl alcohol, 3-pentanol, 2-methyl-1-butanol, isoamyl alcohol, tert-amyl alcohol, 3-methyl-2-butanol, or neopentyl alcohol. These alcohols may be used alone or in combination.
  • Examples of the ketone having 3 to 5 carbon atoms include acetone, methyl ethyl ketone, and diethyl ketone. These ketones may be used alone or in combination.
  • the solvent is preferably methanol or ethanol. This is because it is easy to remove later. Further, it is preferable to use the same solvent as that produced by the reaction between the fatty acid ester and the alkali metal salt. For example, when a fatty acid alkyl ester having a methyl group or an ethyl group is reacted with an alkali metal hydroxide, it is preferable to use methanol or ethanol as a solvent.
  • this solvent does not contribute to the reaction, the amount of use thereof is arbitrary as long as the alkali metal salt is dissolved.
  • stirring may be performed or stirring may not be performed. Further, it may be heated or not heated during the dissolution.
  • the fatty acid ester is preferably dissolved.
  • the fatty acid ester may be melted or dissolved, for example.
  • the fatty acid ester is solid at room temperature, the fatty acid ester previously melted or dissolved in a solvent may be mixed with the alkali metal salt solution, or the solid fatty acid ester is a solution of the alkali metal salt. It may melt after being mixed with.
  • the solid fatty acid ester may be melted by being heated to a melting point or higher, or the solid fatty acid ester is a non-polar solvent such as alcohol, ketone, hexane or heptane.
  • the solid fatty acid ester may be dissolved in an organic solvent.
  • it may be heated or may not be heated.
  • the heating performed when the solid fatty acid ester is melted or dissolved in a solvent may or may not be performed by microwave irradiation.
  • a fatty acid alkali metal salt When a fatty acid ester and a solution in which an alkali metal salt is dissolved in a solvent are mixed and heated, a fatty acid alkali metal salt can be generated.
  • microwaves are preferably used for heating, but this need not be the case. It is preferable to perform refluxing during the heating.
  • the heating temperature is not particularly limited, but is preferably in the range of 30 ° C. to 200 ° C., more preferably 60 ° C. or higher.
  • the heating time is not particularly limited, but is preferably in the range of 5 minutes to 24 hours, more preferably in the range of 20 minutes to 2 hours, and still more preferably in the range of 30 minutes to 1 hour. Moreover, it is suitable to make it react under reduced pressure.
  • the pressure may be reduced or normal pressure.
  • the pressure reduction may be started together with the heating.
  • the pressure is preferably reduced to 1 to 90 kPa by decompression, more preferably 1 to 10 kPa, and further preferably 1 to 4 kPa.
  • Examples of the alkali metal of the fatty acid alkali metal salt produced by the reaction are as described above, and examples of the fatty acid are also as described above.
  • the fatty acid alkali metal salt to be produced for example, potassium caprylate, potassium caprate, potassium laurate, potassium myristate, potassium palmitate, potassium palmitate, potassium stearate, potassium oleate, potassium linoleate
  • the fatty acid alkali metal salt may or may not contain an unreacted fatty acid ester. It is preferable to lower the temperature after the reaction is completed. Although the temperature after the fall is not particularly limited, for example, it is preferably less than 100 ° C. or higher than the melting point of the unreacted fatty acid ester.
  • the basic catalyst is not particularly limited as long as it is a basic catalyst, but may be, for example, an alkali metal salt, an alkaline earth metal salt, or a metal salt.
  • the alkali metal salt is a salt of an alkali metal such as lithium, sodium, or potassium.
  • the alkaline earth metal salt is, for example, a salt of an alkaline earth metal such as beryllium, magnesium, or calcium.
  • the metal salt is a salt of a metal such as manganese, zinc, copper, or nickel.
  • the salt may be, for example, a hydroxide, carbonate, bicarbonate, hydride, or alkoxide, as described above.
  • the alkali metal salt is not particularly limited, and may be, for example, potassium hydroxide, potassium carbonate, potassium hydrogen carbonate, methoxy potassium, sodium hydroxide, sodium carbonate, sodium hydrogen carbonate, or sodium methoxide.
  • the alkaline earth metal salt is not particularly limited, and may be, for example, magnesium hydroxide, magnesium carbonate, magnesium hydrogen carbonate, magnesium methoxide, calcium hydroxide, calcium carbonate, calcium hydrogen carbonate, or calcium methoxide.
  • a metal salt is not specifically limited, For example, manganese hydroxide or zinc hydroxide may be sufficient.
  • These basic catalysts may be used alone or as a mixture of two or more. This basic catalyst is at least partially soluble in water.
  • this basic catalyst can also be called a water-soluble catalyst.
  • a basic catalyst that is completely soluble in water.
  • this basic catalyst is used in esterification of the hydroxyl group of sucrose, it can also be called an esterification catalyst.
  • the basic catalyst is preferably the same alkali metal salt as the alkali metal of the fatty acid alkali metal salt.
  • the alkali metal of the fatty acid alkali metal salt is potassium or sodium
  • the basic catalyst is preferably potassium hydroxide or sodium hydroxide.
  • the amount of water in the step of preparing the aqueous solution containing sucrose and the basic catalyst is not limited, but since it is necessary to remove the water later, it is the minimum amount of water in a range where sucrose can be dissolved. Is preferred.
  • the amount of the basic catalyst is preferably in the range of 0.01 to 20% by weight and more preferably in the range of 0.1 to 5% by weight with respect to sucrose.
  • stirring such as rotary stirring or rocking stirring may be performed. In the process, heating may be performed or may not be performed.
  • the order in which sucrose and a basic catalyst are dissolved in water is not ask
  • Examples of fatty acid esters used in the step of producing sucrose fatty acid esters are as described above.
  • the fatty acid ester may be the same as or different from the fatty acid ester used in the step of producing the fatty acid alkali metal salt.
  • an unreacted fatty acid ester that was not used in the reaction in the step of producing the fatty acid alkali metal salt may be used in the step of producing the sucrose fatty acid ester, or The same fatty acid ester may be newly added.
  • the fatty acid ester may be melted or charged or melted after being charged. May be.
  • the fatty acid ester is melted when the sucrose fatty acid ester is produced. If the fatty acid ester used to produce the sucrose fatty acid ester is the same as the fatty acid ester used to produce the fatty acid alkali metal salt, even if an excess amount of fatty acid ester is used relative to sucrose, When the fatty acid ester is recovered and used, there is an advantage that reusability is good because other types of fatty acid esters are not mixed.
  • This fatty acid alkali metal salt is used as an emulsifier in a mixture of an aqueous solution of sucrose and a fatty acid ester.
  • the illustration of the fatty acid alkali metal salt used in the step of producing the sucrose fatty acid ester is as described above, and these fatty acid alkali metal salts may be used singly or in a plurality of mixtures. May be.
  • the amount of fatty acid alkali metal salt used is not particularly limited. For example, it is preferably 1 to 50% by weight based on the total mixture, and the fatty acid ester used in the production of sucrose fatty acid ester is a fatty acid alkyl ester. In some cases, it is more preferably 10 to 30% by weight.
  • sucrose fatty acid ester In the step of producing sucrose fatty acid ester, an aqueous solution in which sucrose is dissolved in water in the presence of a basic catalyst, the fatty acid alkali metal salt produced in the previous step, and the fatty acid ester are mixed and mixed under reduced pressure.
  • the sucrose fatty acid ester is produced by stirring and heating at As a result of this mixing, the mixing order is not limited as long as the aqueous solution, the fatty acid alkali metal salt, and the fatty acid ester are mixed.
  • the fatty acid ester should just melt
  • the fatty acid ester when the fatty acid ester is solid at room temperature, the fatty acid ester may be melted by heating, for example. In addition, it is suitable for this liquid mixture not to contain the organic solvent.
  • the fatty acid ester mixed with sucrose in this step is preferably in the range of 1 to 20 equivalents per 1 equivalent of sucrose. Thus, the amount of fatty acid ester used is preferably the same or excessive amount as sucrose.
  • the stirring performed in this step may be, for example, rotational stirring, rocking stirring, ultrasonic stirring, or any combination of two or more thereof. The stirring may be performed continuously or intermittently.
  • a mixture obtained by mixing an aqueous solution of sucrose, a fatty acid alkali metal salt, and a fatty acid ester is a fluid having a high viscosity. Therefore, this mixture can also be considered as a highly viscous liquid mixture.
  • the step of producing a sucrose fatty acid ester has a preceding step of removing water from the mixture, and a subsequent step of performing transesterification in a state where water is removed after the preceding step.
  • the preceding step it is preferable that sufficient stirring is performed in order to remove water in a state where the dispersoid which is an aqueous solution of sucrose is uniformly dispersed.
  • the subsequent step it is preferable that sufficient stirring is performed from the viewpoint of promoting transesterification between sucrose and a fatty acid ester.
  • the heating in the previous step in the step of producing the sucrose fatty acid ester may or may not be performed by irradiation with microwaves.
  • the heating of the latter process in the process of producing the sucrose fatty acid ester is performed by irradiating with microwaves.
  • the frequency of the microwave is not particularly limited.
  • the frequency may be 2.45 GHz, 5.8 GHz, 24 GHz, 915 MHz, or other 300 MHz to 300 GHz. A frequency within the range may be used.
  • the microwave of a single frequency may be irradiated and the microwave of a several frequency may be irradiated.
  • microwaves having a plurality of frequencies may be irradiated at the same time, or may be irradiated at different times.
  • microwaves with multiple frequencies are irradiated at different times, for example, microwaves with frequencies that are easily absorbed by the raw material are irradiated at the start of the reaction, and the product is absorbed at the time when the reaction proceeds.
  • Microwaves with a frequency that can be easily applied may be irradiated.
  • microwaves having a plurality of frequencies may be irradiated at the same position or may be irradiated at different positions.
  • microwaves of a plurality of frequencies are respectively irradiated at different positions, for example, at a position on the upstream side of the flow type reactor, that is, at a position where the ratio of the raw material is higher than that of the product
  • Microwaves may be irradiated, and microwaves having a frequency that is easily absorbed by the product may be irradiated at a position downstream of the reactor, that is, at a position where the ratio of the product is higher than that of the raw material.
  • the microwave irradiation may be performed continuously, or may be performed intermittently between irradiation and pause.
  • Irradiation with microwaves raises the temperature of the object to be irradiated, but the intensity of microwave irradiation may be adjusted so that the temperature remains constant. Well, or the intensity of microwave irradiation may be changed in small increments.
  • the temperature of the mixture to be irradiated with the microwave may be measured using a known thermometer such as a thermocouple thermometer or an infrared optical fiber thermometer. The measured temperature may be used to control the output (intensity) of the microwave.
  • the microwave irradiation may be performed in a single mode or in a multimode.
  • the catalyst which has a microwave absorptivity may be injected
  • the produced sucrose fatty acid ester is used for foods and pharmaceuticals and the catalyst needs to be completely removed after the reaction, it is preferable not to use the catalyst.
  • the temperature of the first step is preferably lower than the reaction temperature of the second step, that is, the step of transesterification. If the temperature in the previous step is the same as or higher than the reaction temperature in the subsequent transesterification step, the transesterification starts in the previous step, resulting in a low yield of sucrose fatty acid ester in the subsequent step. Because it becomes. On the other hand, if the temperature of the preceding step is too low, water cannot be removed, and the reaction in the subsequent step is hindered. Therefore, it is preferable that the temperature of the mixture in the preceding step is higher than room temperature and lower than the reaction temperature in the subsequent step.
  • the previous step it is preferably heated in the range of 40 ° C. to 80 ° C., more preferably in the range of 50 ° C. to 80 ° C.
  • the time of the preceding step is preferably in the range of 5 minutes to 24 hours, more preferably in the range of 20 minutes to 2 hours, and in the range of 30 minutes to 1 hour. Is more preferred.
  • the removal of water is preferably performed until the amount of remaining water is 0.1 to 2% by weight based on the entire mixture.
  • the mixture is heated so that it is lower than the decomposition temperature of sucrose.
  • the sucrose decomposition temperature is a temperature at which sucrose decomposition begins.
  • the decomposition temperature at which sucrose odors when heated for a short time begins around 135 ° C.
  • the heating is performed in a range lower than the decomposition temperature of sucrose by 25 ° C. to a range lower than the decomposition temperature of sucrose, and a temperature lower by 10 ° C. than the decomposition temperature of sucrose.
  • the mixture is preferably heated to a range of 100 ° C. to 135 ° C., more preferably 110 ° C. to 133 ° C., and a range of 110 ° C. to 130 ° C. More preferably it is heated.
  • the mixture may be heated to 120 ° C. or higher.
  • heating by microwaves may be performed so that the measurement temperature of the mixture becomes “decomposition temperature of sucrose ⁇ (° C.)”.
  • ⁇ is a positive real number. Note that ⁇ is preferably a small value, but the value of ⁇ may be selected in accordance with the responsiveness of feedback of temperature control using microwaves. Specifically, the value of ⁇ may be decreased when the responsiveness is high, and the value of ⁇ may be increased when the responsiveness is low.
  • the reaction time (heating time) in the subsequent step is preferably 5 minutes to 6 hours. In addition, the minimum of the reaction time may be 30 minutes or more, for example, and may be 1 hour or more. Further, the upper limit of the reaction time may be, for example, 6 hours or less, 5 hours or less, 4 hours or less, 3.5 hours or less, 3 It may be less than time.
  • the time of the subsequent step is about the time when the yield of the monoester reaches a peak.
  • the temperature may be constant or may vary. In the latter case, for example, the mixture may be heated so as to increase the temperature in the subsequent step of performing the transesterification.
  • the temperature increase may be performed, for example, by a linear temperature change, may be performed by a step-like temperature change, or may be another temperature increase.
  • the temperature increases monotonously in the subsequent stage, but as the entire period of the subsequent stage It is sufficient that the temperature rises, and there may be a period during which the temperature falls microscopically. This is because, for example, such a situation can occur when the microwave is intermittently irradiated.
  • the temperature changes in the subsequent steps it is important that the temperature does not exceed the decomposition temperature of sucrose.
  • the produced sucrose fatty acid ester it is suitable that there is much content rate of a monoester.
  • the weight ratio of the monoester is preferably larger than the weight ratio of the sucrose fatty acid ester in which two or more hydroxyl groups of sucrose are esterified with the fatty acid ester.
  • the weight ratio of the monoester is preferably 60% by weight or more, more preferably 70% by weight or more, and 80% by weight or more. More preferably it is.
  • Monoesters of sucrose fatty acid esters are known to have antibacterial properties, and those with a higher monoester content are more soluble in water, so sucrose fatty acid esters are used, for example, in foods and beverages. This is because, in some cases, a high monoester content is required.
  • high-purity monoesters may be required for uses such as pharmaceuticals. In such cases, it is better to purify high-purity monoesters from those with a high monoester content.
  • the proportion of monoester is high.
  • the heating time is preferably 3 hours or less. More preferably, it is 2.5 hours or less.
  • the heating time is preferably 4 hours or less, and 3.5 hours or less. Is more preferred.
  • generated sucrose fatty acid ester is high. In the present invention, such high monoester selectivity and high yield could be achieved by microwave heating.
  • the pre-stage and post-stage pressures are preferably 1 to 90 kPa, and more preferably 1 to 10 kPa.
  • the pressure may be the same in the preceding process and the subsequent process, or may vary. In the latter case, for example, the pressure in the subsequent process may be higher than the pressure in the previous process.
  • the degree of decompression may be within a range in which the raw material (for example, fatty acid ester or the like) does not vaporize.
  • sucrose fatty acid ester is produced by transesterification in the step of producing sucrose fatty acid ester.
  • the sucrose fatty acid ester is not particularly limited.
  • the mixture may be cooled after transesterification. This is to prevent the monoester from becoming a diester.
  • a normal method can be used as a method for extracting the produced sucrose fatty acid ester.
  • an organic solvent for example, methyl ethyl ketone, water-insoluble alcohol, etc.
  • the organic solvent includes unreacted fatty acid ester and sucrose fatty acid ester.
  • the water contains unreacted sucrose and fatty acid alkali metal salts.
  • the sucrose fatty acid ester can be extracted by crystallizing and extracting the sucrose fatty acid ester from the organic solvent.
  • sucrose fatty acid ester As described above, according to the method for producing a sucrose fatty acid ester according to the present invention, in the subsequent step in the step of producing the sucrose fatty acid ester, by heating the mixture to be lower than the decomposition temperature of sucrose, A sucrose fatty acid ester having no odor can be produced. Further, by heating with microwaves, it becomes possible to obtain a sucrose fatty acid ester having a high monoester selectivity and high yield in a short time. In addition, since no harmful organic solvent is used in the step of producing a sucrose fatty acid ester, a sucrose fatty acid ester suitable for foods, pharmaceuticals, and cosmetics can be produced.
  • the method for producing a sucrose fatty acid ester includes a step of producing a fatty acid alkali metal salt is described, but this need not be the case.
  • the fatty acid alkali metal salt may be used in the step of producing a sucrose fatty acid ester.
  • the fatty acid alkali metal salt may be produced by a method different from the above description.
  • Example 1 Method for producing sucrose palmitate [Example 1] A three-necked flask was charged with 98 g of methyl palmitate heated to 60 ° C. and melted and a solution of 3.8 g of potassium hydroxide dissolved in 30 ml of methanol. After placing the three-necked flask in a microwave reactor ( ⁇ Reactor EX, manufactured by Shikoku Keikaku Kogyo Co., Ltd.) equipped with a stirrer and a thermometer, the microwave was irradiated with 2.45 GHz microwave and heated to 100 ° C. while stirring. Reflux was performed for a minute. Thereafter, the temperature was maintained at 100 ° C.
  • ⁇ Reactor EX manufactured by Shikoku Keikaku Kogyo Co., Ltd.
  • Example 2 Sucrose palmitate was produced in the same manner as in Example 1 except that the time for transesterification was changed from 1 hour to 2 hours. Also in this case, there was no coloring or odor from the start of the reaction to the end of the reaction. The results are as shown in FIG.
  • Example 3 Sucrose palmitate was produced in the same manner as in Example 1 except that the time for transesterification was changed from 1 hour to 3 hours. Also in this case, there was no coloring or odor from the start of the reaction to the end of the reaction. The results are as shown in FIG.
  • Example 4 Sucrose palmitate was produced in the same manner as in Example 2 except that the temperature during the transesterification reaction was changed from 120 ° C to 110 ° C. Also in this case, there was no coloring or odor from the start of the reaction to the end of the reaction. The results are as shown in FIG.
  • Example 5 Sucrose palmitate was produced in the same manner as in Example 4 except that the transesterification time was changed from 2 hours to 4 hours. Also in this case, there was no coloring or odor from the start of the reaction to the end of the reaction. The results are as shown in FIG.
  • Example 6 Sucrose palmitate was produced in the same manner as in Example 2 except that the temperature during the transesterification reaction was changed from 120 ° C to 100 ° C. Also in this case, there was no coloring or odor from the start of the reaction to the end of the reaction. The results are as shown in FIG.
  • Example 7 The temperature of the transesterification reaction was 110 ° C. for the first half hour and 120 ° C. for the first half hour, and the transesterification reaction was carried out for a total of 2 hours. Generated. In addition, the temperature increase from 110 ° C. to 120 ° C. was performed immediately, and the degree of vacuum was maintained at that time. Also in this case, there was no coloring or odor from the start of the reaction to the end of the reaction. The results are as shown in FIG.
  • Example 1 Sucrose palmitate was produced in the same manner as in Example 2, except that heating by microwave irradiation was changed to heating by an oil bath (conventional heating). In this case, the reaction solution colored brownish brown during the transesterification reaction and had a burnt sucrose smell. The results are as shown in FIG. Even when the temperature during the transesterification reaction was changed from 120 ° C. to 110 ° C., the reaction solution was colored brown as in Comparative Example 1.
  • FIG. 2 is a graph showing the change over time in the monoester yield and the weight ratio of the monoester in Examples 1 to 3 and Comparative Examples 2 to 4.
  • a monoester is produced, a diester is produced from the monoester, and a triester is produced from the diester.
  • the yield of the monoester gradually increases with the passage of time and starts to decrease from the middle.
  • the diester etc. are produced
  • the time change of the yield of the monoester in microwave heating is shortened by less than 1/2 with respect to the time change of the yield of monoester in the conventional heating (CH).
  • the weight ratio (83%) of the monoester of Comparative Example 3 is smaller than the weight ratio (85%) of the monoester of Example 1.
  • the yield of the monoester is more in the time direction than the proportion of the monoester. It can be seen that is shortened shorter. Due to the existence of such differences, microwave heating can simultaneously achieve a high yield of monoester and a high selectivity in a short reaction time range (for example, a reaction time within 4 hours). become.
  • Example 7 it can be seen that a higher yield of monoester and a higher selectivity of monoester can be achieved by increasing the reaction temperature stepwise during the transesterification reaction. Therefore, it is considered that a higher yield of monoester and a higher selectivity of monoester can be compatible by heating the mixture so that the temperature of the mixture is increased during the transesterification reaction.
  • the time for the transesterification reaction (that is, the heating time in the subsequent step) may be the time for which the yield of the monoester reaches a peak.
  • the time when the yield of the monoester reaches a peak should theoretically be one point in time, but in reality it is difficult to specify the point. Therefore, the time when the yield of the monoester reaches a peak may be considered as a period having a width.
  • the time for the transesterification reaction in which the monoester yield peaks in microwave heating at 120 ° C. (Examples 1 to 3) may be considered to be in the range of 1.5 hours to 2.5 hours. Good.
  • reaction temperature the higher the yield of the monoester can be realized in the range below the decomposition temperature of sucrose. Therefore, it can be seen that the reaction is preferably performed at a reaction temperature closer to the decomposition temperature of sucrose.
  • the content was cooled to 80 degreeC.
  • the content is a mixture of 88.3 g methyl stearate and 21.9 g potassium stearate.
  • An aqueous solution in which 12 g of sucrose and 0.5 g of potassium hydroxide were dissolved in 8 g of water was charged into the three-necked flask. While stirring the mixture in the three-necked flask, the pressure was reduced while stirring, and the pressure was reduced to 4 kPa to evaporate water.
  • Example 9 Sucrose stearate was produced in the same manner as in Example 8 except that the time for the transesterification reaction was changed from 1 hour to 2 hours. Also in this case, there was no odor from the start of the reaction to the end of the reaction. The results are as shown in FIG.
  • Example 10 Sucrose stearate was produced in the same manner as in Example 8 except that the time for the transesterification reaction was changed from 1 hour to 3 hours. Also in this case, there was no odor from the start of the reaction to the end of the reaction. The results are as shown in FIG.
  • Example 11 Sucrose stearate was produced in the same manner as in Example 8 except that the time for transesterification was changed from 1 hour to 4 hours. Also in this case, there was no odor from the start of the reaction to the end of the reaction. The results are as shown in FIG.
  • Example 12 Sucrose stearate was produced in the same manner as in Example 8 except that the temperature during the transesterification reaction was changed from 130 ° C to 120 ° C. Also in this case, there was no odor from the start of the reaction to the end of the reaction. The results are as shown in FIG.
  • Example 13 Sucrose stearate was produced in the same manner as in Example 12 except that the time for the transesterification reaction was changed from 1 hour to 2 hours. Also in this case, there was no odor from the start of the reaction to the end of the reaction. The results are as shown in FIG.
  • Example 14 Sucrose stearate was produced in the same manner as in Example 12 except that the time for transesterification was changed from 1 hour to 3 hours. Also in this case, there was no odor from the start of the reaction to the end of the reaction. The results are as shown in FIG.
  • Example 15 Sucrose stearate was produced in the same manner as in Example 12 except that the time for transesterification was changed from 1 hour to 4 hours. Also in this case, there was no odor from the start of the reaction to the end of the reaction. The results are as shown in FIG.
  • FIG. 4 is a graph showing the change over time in the yield of monoester and the weight ratio of monoester in Examples 8 to 15 and Comparative Examples 6 to 9.
  • the reaction proceeds such that a monoester is first produced, a diester is produced from the monoester, and a triester is produced from the diester.
  • the change in the yield of 11 the yield of the monoester gradually increases with the passage of time and starts to decrease from the middle.
  • the diester etc. are produced
  • the time for the transesterification reaction (that is, the heating time in the subsequent step) may be the time for which the yield of the monoester reaches a peak.
  • the time when the yield of the monoester reaches a peak should theoretically be one point in time, but in reality it is difficult to specify the point. Therefore, the time when the yield of the monoester reaches a peak may be considered as a period having a width.
  • the time for the transesterification reaction at which the monoester yield peaks in microwave heating at 130 ° C. (Examples 8 to 11) may be considered to be in the range of 2.5 to 3.5 hours. Good.
  • Example 16 Method for producing sucrose caprylate [Example 16] A three-necked flask was charged with 57.5 g of methyl caprylate heated to 60 ° C. and melted and a solution of 3.8 g of potassium hydroxide dissolved in 30 ml of methanol. After placing the three-necked flask in a microwave reactor ( ⁇ Reactor EX, manufactured by Shikoku Keikaku Kogyo Co., Ltd.) equipped with a stirrer and a thermometer, the microwave was irradiated with 2.45 GHz microwave and heated to 100 ° C. while stirring. Reflux was performed for a minute. Thereafter, the temperature was maintained at 100 ° C.
  • ⁇ Reactor EX manufactured by Shikoku Keikaku Kogyo Co., Ltd.
  • the content was cooled to 80 degreeC.
  • the content is a mixture of 46.8 g methyl caprylate and 12.3 g potassium caprylate.
  • An aqueous solution in which 12 g of sucrose and 0.5 g of potassium hydroxide were dissolved in 8 g of water was charged into the three-necked flask. While stirring the mixture in the three-necked flask at 80 ° C., the pressure was reduced and the pressure was reduced to 10 kPa to evaporate water.
  • sucrose caprylate was obtained from the reaction product using acetone.
  • the yield of sucrose caprylate and the proportion of monoester were analyzed by high performance liquid chromatography and gas chromatography. The result is as shown in FIG.
  • Sucrose caprylate was produced in the same manner as in Example 16 except that the time for transesterification was changed from 1 hour to 2 hours, 3 hours, 4 hours, and 6 hours. Also in this case, there was no odor from the start of the reaction to the end of the reaction. The results are as shown in FIG.
  • Sucrose caprylate was produced in the same manner as in Examples 16 to 20, except that the temperature during the transesterification reaction was changed from 130 ° C to 120 ° C. Also in this case, there was no odor from the start of the reaction to the end of the reaction. The results are as shown in FIG.
  • Sucrose caprylate was produced in the same manner as in Examples 16 to 20, except that the temperature during the transesterification reaction was changed from 130 ° C to 110 ° C. Also in this case, there was no odor from the start of the reaction to the end of the reaction. The results are as shown in FIG.
  • Sucrose caprylate was produced in the same manner as in Examples 26 to 30 except that heating by microwave irradiation was changed to heating by an oil bath (conventional heating). In this case, there was no odor from the start of the reaction to the end of the reaction. The results are as shown in FIG.
  • Sucrose caprylate was produced in the same manner as in Comparative Examples 11 to 15 except that the temperature during the transesterification reaction was changed from 110 ° C. to 100 ° C. Also in this case, there was no odor from the start of the reaction to the end of the reaction. The results are as shown in FIG.
  • FIG. 6 is a graph showing the change over time in the yield of monoester and the weight ratio of monoester in Examples 16 to 30 and Comparative Examples 11 to 20.
  • sucrose caprylic acid ester first, a monoester is produced, a diester is produced from the monoester, and a triester is produced from the diester.
  • the change in the yield of 30 the yield of the monoester gradually increases with the passage of time and starts to decrease from the middle.
  • the diester etc. are produced
  • the time for the transesterification reaction (that is, the heating time in the subsequent step) may be the time for which the yield of the monoester reaches a peak.
  • the time when the yield of the monoester reaches a peak should theoretically be one point in time, but in reality it is difficult to specify the point. Therefore, the time when the yield of the monoester reaches a peak may be considered as a period having a width.
  • the time for the transesterification reaction in which the yield of monoester reaches a peak in microwave heating at 130 ° C. may be considered to be in the range of 1.5 hours to 2.5 hours.
  • Examples 16 to 20 and Examples 21 to 25 it can be seen that in the range below the decomposition temperature of sucrose, a higher yield of monoester can be realized at a higher reaction temperature. . Therefore, it is considered that the reaction is preferably performed at a reaction temperature closer to the decomposition temperature of sucrose. Further, in this example, when the heating time in the subsequent step is 6 hours or less, a monoester weight ratio of 70% by weight or more can be realized. In particular, when the heating time in the subsequent step is 4 hours or less, a weight ratio of the monoester of 80% by weight or more can be realized.
  • the content was cooled to 80 degreeC.
  • the contents are a mixture of 63.4 g of methyl laurate and 16.1 g of potassium laurate.
  • An aqueous solution in which 12 g of sucrose and 0.5 g of potassium hydroxide were dissolved in 8 g of water was charged into the three-necked flask. While stirring the mixture in the three-necked flask, the pressure was reduced while stirring, and the pressure was reduced to 4 kPa to evaporate water.
  • Examples 32 to 35 Sucrose laurate was produced in the same manner as in Example 31, except that the time for the transesterification reaction was changed from 1 hour to 2 hours, 3 hours, 4 hours, and 6 hours. Also in this case, there was no odor from the start of the reaction to the end of the reaction. The result is as shown in FIG.
  • Examples 36 to 40 Sucrose laurate was produced in the same manner as in Examples 31 to 35 except that the temperature during the transesterification reaction was changed from 130 ° C to 120 ° C. Also in this case, there was no odor from the start of the reaction to the end of the reaction. The result is as shown in FIG.
  • Example 41 to 45 Sucrose laurate was produced in the same manner as in Examples 31 to 35 except that the temperature during the transesterification reaction was changed from 130 ° C to 110 ° C. Also in this case, there was no odor from the start of the reaction to the end of the reaction. The result is as shown in FIG.
  • FIG. 8 is a graph showing the change over time in the yield of monoesters and the weight ratio of monoesters in Examples 31 to 45 and Comparative Examples 21 to 30.
  • a monoester is produced, a diester is produced from the monoester, and a triester is produced from the diester.
  • the change in the yield of 45 the yield of the monoester gradually increases with the passage of time and starts to decrease from the middle.
  • the diester etc. are produced
  • the time change of the monoester ratio in the microwave heating is not shortened to 1/12 with respect to the time change of the monoester ratio in the conventional heating.
  • the weight ratio (91.9%) of the monoester of Comparative Example 25 is smaller than the weight ratio (97.4%) of the monoester of Example 31.
  • the yield of the monoester is more in the time direction than the proportion of the monoester. It can be seen that is shortened shorter. Due to the existence of such differences, microwave heating can simultaneously achieve a high yield of monoester and high selectivity in a short reaction time range (for example, a reaction time range of 6 hours or less). become.
  • the time for the transesterification reaction may be the time for which the yield of the monoester reaches a peak.
  • the time when the yield of the monoester reaches a peak should theoretically be one point in time, but in reality it is difficult to specify the point. Therefore, the time when the yield of the monoester reaches a peak may be considered as a period having a width.
  • the time for the transesterification reaction in which the yield of monoester reaches a peak in microwave heating at 130 ° C. may be considered to be in the range of 1.5 hours to 2.5 hours.
  • Examples 31 to 35 and Examples 36 to 40 it can be seen that a higher yield of monoester can be realized at a higher reaction temperature within a range below the decomposition temperature of sucrose. . Therefore, it is considered that the reaction is preferably performed at a reaction temperature closer to the decomposition temperature of sucrose. Further, in this example, when the heating time in the subsequent step is 6 hours or less, it is possible to realize a monoester weight ratio of 65% by weight or more. In particular, when the heating time in the subsequent step is 4 hours or less, a weight ratio of the monoester of 75% by weight or more can be realized.
  • Example 46 Method for producing sucrose oleate [Example 46] A three-necked flask was charged with 107.8 g of methyl oleate heated to 60 ° C. and melted, and a solution of 3.8 g of potassium hydroxide dissolved in 30 ml of methanol. The three-necked flask was placed in a microwave reactor ( ⁇ Reactor EX, manufactured by Shikoku Keiki Kogyo Co., Ltd.) equipped with a stirrer and a thermometer, and then irradiated with 2.45 GHz microwave, heated to 100 ° C. while stirring, Reflux was performed for a minute. Thereafter, the pressure was maintained at 100 ° C.
  • ⁇ Reactor EX manufactured by Shikoku Keiki Kogyo Co., Ltd.
  • Example 47 Sucrose oleate was produced in the same manner as in Example 46 except that the time for the transesterification reaction was changed from 1 hour to 2 hours, 3 hours, 4 hours, and 6 hours. Also in this case, there was no odor from the start of the reaction to the end of the reaction. The result is as shown in FIG.
  • Example 51 to 55 Sucrose oleate was produced in the same manner as in Examples 46 to 50 except that the temperature during the transesterification reaction was changed from 130 ° C to 120 ° C. Also in this case, there was no odor from the start of the reaction to the end of the reaction. The result is as shown in FIG.
  • Example 56 to 60 Sucrose oleate was produced in the same manner as in Examples 46 to 50 except that the temperature during the transesterification reaction was changed from 130 ° C to 110 ° C. Also in this case, there was no odor from the start of the reaction to the end of the reaction. The result is as shown in FIG.
  • FIG. 10 is a graph showing the change over time in the yield of monoester and the proportion by weight of monoester in Examples 46 to 60 and Comparative Examples 31 to 40.
  • sucrose oleate first, a monoester is produced, a diester is produced from the monoester, and a triester is produced from the diester.
  • the change in yield of 50 the yield of monoester gradually increases with the passage of time and starts to decrease from the middle.
  • the diester etc. are produced
  • the time change of the conventional heating at 110 ° C. (Comparative Examples 31 to 35) is different from the time change of the conventional heating in Comparative Examples 1 to 30, and the monoester yield in the initial stage of heating is different.
  • the degree of increase is large, and the degree of decrease in the proportion of monoester is also large.
  • the yield of the monoester reached the upper limit in about 3 hours, and the upper limit is lower than the upper limit of the yield of the monoester in microwave heating. Yes.
  • the yield of the monoester in the conventional heating is about half of the yield of the monoester in the microwave heating.
  • the time change of the monoester ratio in the microwave heating generally has a larger value than the time change of the monoester ratio in the conventional heating of Comparative Examples 31 to 35 as a whole. Therefore, microwave heating can achieve a higher monoester yield and higher selectivity than conventional heating at 110 ° C.
  • the time change of the monoester ratio in the microwave heating is not shortened to 1/6 with respect to the time change of the monoester ratio in the conventional heating.
  • the weight ratio (88.4%) of the monoester of Comparative Example 40 is smaller than the weight ratio (91.8%) of the monoester of Example 47.
  • the yield of the monoester is more in the time direction than the proportion of the monoester. It can be seen that is shortened shorter.
  • the time for the transesterification reaction (that is, the heating time in the subsequent step) may be the time for which the yield of the monoester reaches a peak.
  • the time when the yield of the monoester reaches a peak should theoretically be one point in time, but in reality it is difficult to specify the point. Therefore, the time when the yield of the monoester reaches a peak may be considered as a period having a width.
  • the time for the transesterification reaction in which the yield of the monoester reaches a peak in microwave heating at 130 ° C. may be considered to be in the range of 3.5 hours to 5 hours.
  • Examples 46 to 50 and Examples 51 to 55 it can be seen that in the range below the decomposition temperature of sucrose, a higher yield of monoester can be realized at a higher reaction temperature. . Therefore, it is considered that the reaction is preferably performed at a reaction temperature closer to the decomposition temperature of sucrose. Further, in this example, when the heating time in the subsequent step is 6 hours or less, a weight ratio of monoester of 60% by weight or more can be realized. In particular, when the heating time in the subsequent step is 4 hours or less, a weight ratio of monoester of 70% by weight or more can be realized.
  • the contents are a mixture of 87.1 g of methyl linoleate and 21.6 g of potassium linoleate.
  • An aqueous solution in which 12 g of sucrose and 0.5 g of potassium hydroxide were dissolved in 8 g of water was charged into the three-necked flask. While stirring the mixture in the three-necked flask, the pressure was reduced while stirring, and the pressure was reduced to 4 kPa to evaporate water.
  • sucrose linoleic acid ester was obtained from the reaction product using acetone. The yield of sucrose linoleic acid ester and the proportion of monoester were analyzed by high performance liquid chromatography and gas chromatography. The result is as shown in FIG.
  • Example 62 to 65 Sucrose linoleic acid ester was produced in the same manner as in Example 61 except that the time for transesterification was changed from 1 hour to 2 hours, 3 hours, 4 hours, and 6 hours. Also in this case, there was no odor from the start of the reaction to the end of the reaction. The result is as shown in FIG.
  • Example 66 to 70 Sucrose linoleic acid esters were produced in the same manner as in Examples 61 to 65 except that the temperature during the transesterification reaction was changed from 130 ° C to 120 ° C. Also in this case, there was no odor from the start of the reaction to the end of the reaction. The result is as shown in FIG.
  • Example 71 to 75 Sucrose linoleic acid esters were produced in the same manner as in Examples 61 to 65 except that the temperature during the transesterification reaction was changed from 130 ° C to 110 ° C. Also in this case, there was no odor from the start of the reaction to the end of the reaction. The result is as shown in FIG.
  • Sucrose linoleic acid esters were produced in the same manner as in Examples 71 to 75 except that heating by microwave irradiation was changed to heating by an oil bath (conventional heating). In this case, there was no odor from the start of the reaction to the end of the reaction. The result is as shown in FIG.
  • microwave heating can achieve a yield of about 1.8 times that of conventional heating. Yes. In microwave heating, such a high yield can be realized without causing odor.
  • conventional heating since the time change of the yield of the monoester is gradual or the upper limit is low, a high yield of the monoester cannot be realized, but in Examples 61 to 65 and the like, compared to the comparative example Thus, a higher yield can be realized. Particularly in Examples 63 and 64, a high yield and a high weight ratio of the monoester can be realized in a short time.
  • FIG. 12 is a graph showing the change over time in the yield of monoester and the weight ratio of monoester in Examples 61 to 75 and Comparative Examples 41 to 50.
  • sucrose linoleic acid ester first, a monoester is produced, a diester is produced from the monoester, and a triester is produced from the diester.
  • the change in the yield of 65 the yield of the monoester gradually increases with the passage of time and starts to decrease from the middle.
  • the diester etc. are produced
  • the time change of the conventional heating at 110 ° C. (Comparative Examples 41 to 45) is different from the time change of the conventional heating in Comparative Examples 1 to 30, and the monoester yield in the initial stage of heating is different.
  • the degree of increase is large, and the degree of decrease in the proportion of monoester is also large.
  • the monoester yield reached the upper limit in about 2 hours, and the upper limit was lower than the upper limit of the monoester yield in microwave heating. Yes.
  • the yield of the monoester in the conventional heating is about half (about 0.57) of the yield of the monoester in the microwave heating.
  • the time change of the monoester ratio in the microwave heating generally has a larger value than the time change of the monoester ratio in the conventional heating of Comparative Examples 41 to 45. Therefore, microwave heating can achieve a higher monoester yield and higher selectivity than conventional heating at 110 ° C.
  • the time change of the monoester ratio in the microwave heating is not shortened to 1/6 with respect to the time change of the monoester ratio in the conventional heating.
  • the weight ratio (89.8%) of the monoester of Comparative Example 50 is smaller than the weight ratio (90.0%) of the monoester of Example 62.
  • the yield of the monoester is more in the time direction than the proportion of the monoester. It can be seen that is shortened shorter.
  • the time for the transesterification reaction may be the time for which the yield of the monoester reaches a peak.
  • the time when the yield of the monoester reaches a peak should theoretically be one point in time, but in reality it is difficult to specify the point. Therefore, the time when the yield of the monoester reaches a peak may be considered as a period having a width.
  • the time for the transesterification reaction in which the yield of the monoester reaches a peak in microwave heating at 130 ° C. (Examples 61 to 65) may be considered to be in the range of 3.5 hours to 5 hours.
  • Examples 61 to 65 and Examples 66 to 70 it is inferred that higher yields of monoesters can be realized at higher reaction temperatures in the range below the decomposition temperature of sucrose. it can. Therefore, it is considered that the reaction is preferably performed at a reaction temperature closer to the decomposition temperature of sucrose.
  • the heating time in the subsequent step is 6 hours or less, a weight ratio of monoester of 60% by weight or more can be realized.
  • a weight ratio of monoester of 70% by weight or more can be realized.
  • the constituent fatty acids of the fatty acid ester are palmitic acid (16 carbon atoms; saturated fatty acid), stearic acid (18 carbon atoms; saturated fatty acid), caprylic acid (8 carbon atoms; saturated fatty acid), lauric acid (carbon).
  • the number 12 saturated fatty acid
  • oleic acid carbon number 18: monovalent unsaturated fatty acid
  • linoleic acid carbon number 18: polyvalent unsaturated fatty acid
  • sucrose fatty acid esters using fatty acid esters having a fatty acid having 8 to 24 carbon atoms as a constituent fatty acid. Further, it can be inferred that the same effect can be obtained regardless of whether the constituent fatty acid of the fatty acid ester used in the production of the sucrose fatty acid ester is a saturated fatty acid other than the above or an unsaturated fatty acid other than the above. Furthermore, it can be inferred that the same effect can be obtained regardless of the number of unsaturated bonds in the unsaturated fatty acid.
  • the sucrose fatty acid ester obtained by the method for producing a sucrose fatty acid ester according to the present invention can be used, for example, in the fields of food, cosmetics, pharmaceuticals and the like.

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